Cyclic Aromatic Amino Acids with Constrained 1 and 2 Dihedral Angles

互联网2014-02-08

677

The concept of topographic design of peptide neurotransmitters and hormones was pioneered by Hruby ( 1 , 2 ). When the design involved primarily constraint of the side chains of a peptide that has a well-defined backbone conformation, the term “topographic design on a stable template” was proposed ( 3 ). The side chain χ ¹ of aromatic amino acids, such as Phe, Trp, Tyr, and His, can be constrained in either the gauche (−) or gauche (+) conformation by linking the nitrogen atom to the aromatic ring through a methylene bridge (Fig. 1 ).

Fig. 1. Principle of side-chain constraint for Phe, Trp, and His.

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